allyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-> 2)-4-O-acetyl-α-D-fucopyranoside | 201858-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-> 2)-4-O-acetyl-α-D-fucopyranoside
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-2)D-Fuc4Ac(a)-O-allyl；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2S,3R,4S,5R,6R)-5-acetyloxy-4-hydroxy-6-methyl-2-prop-2-enoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 201858-34-6
• 化学式: C₂₅H₃₆O₁₅
• 分子量: 576.552
• InChiKey: VMXUWSZOHRRTLJ-IFNQVJKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  allyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-> 2)-4-O-acetyl-α-D-fucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)

  摘要：

  The first total synthesis of 25(R)-ruscogenin-1-yl beta-D-xylopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->)]-beta-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope musrari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidt's "inverse procedure" is demonstrated. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10536-6
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 allyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-> 2)-4-O-acetyl-α-D-fucopyranoside
  参考文献：
  名称：

  First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)

  摘要：

  The first total synthesis of 25(R)-ruscogenin-1-yl beta-D-xylopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->)]-beta-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope musrari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidt's "inverse procedure" is demonstrated. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10536-6

文献信息

• Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside
  作者：Meizheng Liu、Biao Yu*、Xiangyang Wu、Yongzheng Hui*、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(00)00244-5

  日期：2000.12

  The synthesis of (25R)-ruscogenin-1-yl beta -D-xylopyranosyl-(1 --> 3)-[beta -D-glucopyranosyl-(1 --> 2)]-beta -D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.